


Guy For The Night

by lovingsmutandfluff



Series: Tumblr Ficlets/Drabbles [323]
Category: Supernatural
Genre: Established Jo Harvelle/Anna Milton, F/F, Face-Sitting, Multi, Pegging, Riding, Smut, Strap-Ons
Language: English
Status: Completed
Published: 2015-08-05
Updated: 2015-08-05
Packaged: 2018-04-13 01:29:51
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 886
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4502580
Author URL: https://archiveofourown.org/users/lovingsmutandfluff/pseuds/lovingsmutandfluff
Summary: <blockquote class="userstuff">
              <p>Prompt: Hi, I was wondering if I could request a Jo x Dean x Anna scene? Anna and Jo are dating and want to experiment with adding a guy and they ask Dean since he's their closest male friend.</p>
            </blockquote>





	Guy For The Night

Jo and Anna had been talking about adding a male to their relationship for a while, but neither were sure who to ask.

“What about Dean? Both of us are particularly close to him with our friendships.” Anna recommended.

“Do you think that he’ll accept?” Jo asked.

“It is worth a chance.” Anna replied.

Jo thought about it and nodded.

_

When they had got to Dean, explaining that it was only for the night, and that things might not work out, and if they didn’t, no hard feelings.

“Umm, sure.” Dean said, looking from Jo to Anna. “Yeah, I’ll be your guy for the night.”

Jo and Anna smiled, and nodded, setting up a place and a time for the three to meet.

_

When Dean walked into the motel room that Anna and Jo agreed on, he opened the door, to find both women already naked, Jo over Anna, rubbing and rutting.

Anna’s hands were tangled in Jo’s hair, Jo’s hands latched onto Anna’s shoulders as she sucked on Anna’s neck.

Dean froze unsure of what to do, watching the scene before him.

He must have made a noise because Anna and Jo suddenly turned to look at Dean.

“Whatcha waiting for, Winchester?” Jo asked, shifting so that she was straddling Anna. “Get your ass over here. And strip as you go.” Jo said.

Dean’s eyes drifted to Jo, seeing the strap on that she had on, and a pang of excitement went through him.

He started to strip, slowly walking over to the two on the bed. Jo moved out of the way, and Dean straddled Anna, feeling Jo move behind him.

Dean started to work Anna over, hands brushing her softly. He leaned down, taking one of Anna’s nipples in his mouth and he started sucking, tongue flicking on it, and he heard Anna moan.

Jo grinned, reaching around Dean, and fisting his cock, stroking slowly, and Dean groaned, rocking his hips, fucking himself in Jo’s hand.

“That’s it Dean.” Jo murmured encouragingly. “Fuck, just like that, Dean.”

Dean’s mouth left Anna’s nipple and he started to kiss around Ann’s chest, shoulders, and neck, hands rubbing against Anna, giving her caressing touches.

He felt Jo pull away and heard a foil wrinkling, before he felt Jo slip something on his cock. Dean pulled away and looked down to see a condom rolling on and he looked back at Jo.

“Fuck her, Dean. Nice and slow and deep.”

Dean nodded, and turned back to Anna, spreading her legs and lining himself up. He sank in slowly and watched Anna moan again.

He heard a small  _click_  of a cap opening, and suddenly Dean felt cold, lubed fingers at his hole.

“Jo?” Dean asked, looking back.

Jo looked up at him, and smiled. “You OK with this Dean?” Jo asked.

Dean nodded and turned back to Anna, rocking softly, and relaxing, letting Jo’s fingers enter.

Anna gripped Dean’s shoulders, as Dean’s lips went back to Anna’s neck, as he rocked into Anna and back on Jo’s fingers.

Slowly, he felt himself get open up, the burn from Jo stretching and scissoring turning into pleasure.

“Jo…” Dean groaned. “Fuck….”

“Alright Winchester.” Jo grinned. Jo’s fingers left, leaving Dean open and empty, and he grunted, hands tangling in Anna’s hair, face pressed into her neck, as he sucked and licked.

Suddenly, Dean felt the dildo slide inside him, lubed up and he shuddered, grunting, as he started to fuck himself on the dildo inside him, and fuck Anna.

One of Jo’s hands roamed up Dean’s back, reaching around and tugging on a nub, as he other hand reached around his waist and started rubbing against Anna’s clit.

Pants and moans filled the room, as Dean’s pace started to become more erratic.

“Anna…Jo…gonna…oh, shit…I’m gonna come.” Dean groaned.

“Then come, Dean.” Anna whispered in his ear. Dean seized slightly, and he groaned loudly when he came in the condom.

He felt Anna’s grip on him tighten, and she came on his cock.

Jo pulled away and helped pull Dean out, getting him to lie down. She removed the strap on, and settled on his face, facing Anna, and Dean’s arms wrapped around her thighs and he started sucking and licking, tongue dipping in Jo’s folds and around her clit.

Anna moved, sinking back down on Dean’s cock, and Dean groaned.

Jo shifted slightly over Dean and leaned forward, kissing Anna, as the two rode Dean.

Dean ate out Jo, hips jerking, trying to meet Anna’s thrusts, and he swallowed down what he could, when Jo came.

The two girls pulled off of Dean and moved close to Dean, licking Jo’s juices off his face.

Dean groaned and panted, trying to catch his breath.

When the two pulled away, he felt Anna pull his condom off, tying it and tossing it into the trash.

“Was…was that good?” Dean asked, looking fro Jo to Anna. “Did I do good?”

“Yes, you did.” Anna nodded, leaning down to nibble softly against Dean’s neck. One of Jo’s hand softly ran on Dean’s chest, and he grunted.

“Good job, Dean.” Jo murmured, in his ear. “Wanna relax a little?”

Dean nodded, and Jo laughed. The two girls relaxed by Dean, and the three cuddled on the bed.


End file.
